Dimethylformamide → HCID 86590660, compound

HRID 392443Notes

Reaction equation

HRID 392443 reaction equation
[H-].[Na+].OC1C=C([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)C=CC=1.Br[CH:19]1[CH2:22][CH2:21][CH2:20]1.CN([CH:26]=[O:27])C>>[CH:19]1([O:27][C:26]2[CH:11]=[C:12]([C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[CH2:11][NH2:10])[CH:17]=[CH:16][CH:15]=2)[CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 78110BromocyclobutaneHCID 506616HCID 506616, compound

Product 1

HCID 86590660HCID 86590660, compound

Procedure

Sodium hydride (60% in mineral oil, 0.072 g, 1.8 mmol) was suspended in DMF at 0° C. To the dispersion was added dropwise N-(3-hydroxyphenyl)pyrid-3-ylmethylamine (0.250 g, 1.24 mmol) as a solution in DMF. The reaction mixture was stirred at room temperature for 30 min. Then bromocyclobutane (0.25 g, 1.84 mmol) was added as a solution in DMF. The reaction was concentrated and the residue was diluted with water, extracted with EtOAc, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica-gel chromatography to give N-(4-(3-Cyclobutyloxyphenyl)pyrid-3-ylmethylamine. 1H NMR:, 8.61 (d,1H,J=2.3 Hz), 8.51 (q,1H,J=1.6, 3.13), 7.68 (m,1H), 7.25 (m,1H), 7.04 (t,1H,1.7 Hz), 6.18-6.24 (m,2H), 6.09 (t,1H,J=2.3 Hz), 4.6 (quint,1H,J=6.7 Hz), 2.33-2.42 (m,2H,), 2.06-2.18 (m,2H), 1.76-1.88 (m,1H), 1.57-1.70 (m,1H). MS calcd. 254.1; MS (M+1) 255.1.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-8629fd6d2e8c413d87561582f315d891
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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